


Courtesan

by HLBrennan



Series: Serendipity [1]
Category: Once Upon a Time (TV)
Genre: Alternate Universe - Prostitution, Dirty Talk, F/F, Shameless Smut
Language: English
Status: Completed
Published: 2016-09-06
Updated: 2016-09-06
Packaged: 2018-03-16 12:03:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,598
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3487565
Author URL: https://archiveofourown.org/users/HLBrennan/pseuds/HLBrennan
Summary: <blockquote class="userstuff">
              <p>(n.) a prostitute, especially one with wealthy or upper-class clients</p>
            </blockquote>





	Courtesan

"Are you sure you're up for this, Swan," André asked seriously, running his fingers through Emma's thick waves.

The blonde smiled softly and rolled her eyes, "She's just a woman," she chuckled, leaning closer into the mirror while applying gracious amounts of mascara. "And between you and me, I've been with plenty of women, André."

Emma enjoyed messing with him in such a manner, even if he wasn't playing for the same team. And of course a lesbian would have a gay best friend, who just so happened to be wonderful at matching color pallets and hairstyles with face shapes. Sometimes, she underestimated the man's abilities, but Emma was a product of his capabilities.

When she had first started at the company,  _Carmen Enterprises_ , she was a mess. Emma Swan didn't even know the difference between foundation and concealer, and that was her first lesson from André. On top of primping the girls before they left, André was also a partial owner of the company, along with his partner Jasper. Emma had gotten close to both of them over the short six months she had worked at _Carmen_ , and she wouldn't trade them for the world. 

"That's not what I mean, Em," the man all but whined, producing a brush and beginning to tackle Emma's mane of hair.

Emma closed up her mascara and shook her head. André was overreacting, as usual, over yet another client. As far as the blonde knew, this client was just a woman. Well, a wealthy woman at that, but that didn't matter. All that Emma was concerned about was if said woman was a psychopath and how well this she was paying the blonde for her  services. She was just another woman to the blonde, another paying customer.

Emma laughed softly once again, "Then please," she drawled, a Cheshire grin on her lips as she snatched the brush away, "enlighten me, André."

"This is Miss Regina Mills we're talking about! She's not like the other women you've been with. She's all business."

Nodding her head, Emma brushed through her golden tresses, then plugged in her curling iron. "And how is she any different?  _Miss Mills_ is just like every other career-oriented, influential woman I've been with. I think I can handle her."

"Get it through your hard head, Swan, Miss Mills may seem like the others, but she isn't. She's been through at least five other escorts of ours, and she's sent each away without so much as a kiss." André reached for various clips from his pulled back dreadlocks and sectioned carefully Emma's hair.

The call girl was slightly jealous of her friend's hair; mainly because he could work every hairstyle possible and the fact that it was incredibly shiny, but nonetheless, she was jealous.

While André began curling her hair, Emma grabbed various shades of lipstick and held it up to her skin. "She still payed them, so either way, that's a good day," she hummed, "Which shade would look better."

The man stopped for a moment and peered over her shoulder, raising his eyebrow in question. "Go for the burgundy. It's classy, and you need as much class as you can get."

Emma ignored the quip and rolled her light green eyes. She lined her lips with an even darker shade of red, and then filled the rest with the crimson shade, smacking her lips quickly. The blonde had to admit, the shade complimented her skin tone beautifully. And maybe it made Emma seem classy, but she wouldn't admit that aloud.

"What are you planning on wearing?" He asked casually, yet seemed extremely focused on curling golden strands and removing pins.

"I don't know. Maybe that red dress from Ruby's party last week?"

Emma looked at André in the mirror, noticing that he had stopped what he was doing and now was staring at her. He raised his eyebrow at the blonde, nostrils flaring softly. She knew this look. Either he was confused, or he was disapproving. Emma decided the latter.

"Let me reassert my previous point, darling. Miss Mills is a classy woman. She would not be interested in an escort resembling that of a underpaid whore. She has expensive tastes to say the least, not like a blame her." The darker man continued to primp her hair, pins falling and curls cascading down Emma's back.

The blonde wanted to 'reassert her point' too, but she knew better than to argue with André. So, she kept her lips shut about the topic and decided to ask a question instead. "What should I wear then?"

"Do you still have that evening gown I got you?"

Emma nodded once, watching the reflection of André in the mirror as he curled each strand with intense focus. "The black one?"

"Exactly!" He smiled, taking down the rest of her hair and continuing. "Wear that. It'll look amazing on you."

Blushing slightly, Emma dropped her head down slightly to cover her face, but immediately received a tug on her hair.

"Head up! I'm almost done."

Not long after, Emma's hair was slung across her left shoulder in delicate, princess curls, effortlessly cascading down the dark fabric of her dress. She glanced at herself in the mirror, André positioned behind her, as she took in her whole outfit, minus the shoes that were covered by the dress.

The black gown clung to Emma's hips and thighs, but fell straight to her legs, leaving everything belong her knee to the imagination. Each sleeve was virtually see-through. A presentable, sweetheart neckline was cut at the top of the dress and replaced by the same material as the sleeves, tinting the blonde's covered skin with a light grey. She was speechless as she stared, but Emma had to admit she looked hot, and definitely much better than if she wore her red dress.

"You look dressed to kill," André exclaimed, showing off his pearly teeth. "If I wasn't gay, I would eat you up!"

Emma chuckled, holding her hand over her stomach. "I'm flattered," she teased, "at least I know I'm hot enough to get a gay guy's attention."

"You're more than that, Swan. Now get your pretty ass to that hotel and work your magic!"

The drive to the hotel was short lived, and every mile Emma drove, nerves began to coagulate in her. Her palms were sweating on the steering wheel, and she was sure that this was it. There was no way she could do this. Sure, she had been with countless women, especially the refined, female politicians of the Boston area, but the way that André was describing Miss Mills worried her. If the woman wasn't afraid to send those other girls away, one being Emma's best friend Ruby, then how could Emma be sure that she would not suffer the same fate?

It wasn't like she absolutely wanted to have sex with a random politician, but she has heard things about the infamous Regina Mills. She had seen the woman's face on the front page of a newspaper one day, which one Emma wasn't entirely sure, but she saw the woman, and there was something about the strong demeanor that Miss Mills emanated that aroused the blonde. Not to mention that the politician was an extremely attractive woman. She couldn't be over the age of thirty five, and that was a rough estimate. It wasn't as if Emma plotted out the woman's life in order to guess age.

Emma would never think that Regina graduated high school at age eighteen, went straight to college for some type of four year degree, which would make her roughly twenty two. Perhaps Regina then got a job, but went back to school a few years later, and after graduating with a better degree, the woman was probably twenty six. She earned her current position as... well whatever she did, and the woman was now thirty, give or take.

But again, Emma didn't figure this out in her head; that would be a little obsessive on her part.

Parking on the street, the blonde sat taking a breath before stepping out of her bug, locking it in the process. She looked both ways across the busy intersection before making her way across. A taxi swerved around her in the blink of an eye, its horn blared as it passed. As graceful and politely as possible, the call girl threw up her hand, middle finger out, and cursed the taxi driver out, despite his or her inability to even acknowledge her. Emma Swan was ever the lady, especially when she was facing the rude taxi drivers in the Boston area.

With a snort of annoyance, the woman continued to walk until she reached the hotel. It was a fancy one at that, Emma knew from experience. She had been here numerous times with numerous women, and each time, she felt out of place. She felt she didn't belong there because, well, she didn't. A female escort, high school dropout and previous orphan had no right to be in a high-end establishment, let alone around these million dollar, give or take, female politicians.

And there was that feeling of self-loathing that Emma was so commonly acquainted with. It become twice as bad when the blonde remembered who she was going to meet. Here she was, getting ready to enter a hotel, then a bedroom, all because of Regina _fucking_ Mills, politician extraordinaire. Not to mention the fact that this woman was so hot and yet so finicky that she refused to sleep with the escorts she paid for for whatever selfish reason.

Emma would kill to be able to have that kind of money. She didn't want to necessarily purchase a night with an escort and then toss them out without sleeping with them, but the thought of being able to do such a thing was nice.

Mills probably lived in a lavish mansion with a husband, maybe a kid or two, and could afford to send each child to college without making a dent in her fortune. And here Emma was struggling to pay rent and working as a, in simplest terms, a higher paid slut.

 _Perfect,_ Emma thought as she walked into the hotel, venom in her self-conscious, _This is just fucking perfect._

Composing herself as much as possible, Emma entered the hotel and immediately went to the front desk. She was sure the receptionist knew her name by now, or at least why she was here so frequently.

"I'm here for a Miss Mills," Emma said softly, keeping her voice low as she spoke to the stereotypical, male receptionist that was just so casually named Doug.

He scanned the blonde up and down for a moment before putting his attention to the monitor in front of him and typing. "Room 451," Doug said simply, keeping his eyes glued to the screen. "And please keep the noise level of your... _activities_ to an adult roar. We do have other guests."

Emma stared at the man in shock at his audacity before she shook herself back to reality. Walking with as much of a stride as she could muster in that dress, Emma stormed to the elevator and sighed in content with the fact that it was empty. How dare he, the damned prick! She would show him the meaning of adult roar when she kicked his ass, that was if she ever got the chance. But, there was no way that would happen with Emma in this dress, so tonight was out of the question.

The elevator opened on the fourth floor, and in no time, Emma was standing in front of room 451. Her palms were sweaty and she was a mixture of anxious and pissed off. That was the perfect mixture of emotions for hot, steamy sex. That was if Regina _I'm too good for female escorts because I'm a self-accomplished woman, but I waste my money on escorts anyhow_ Mills wanted to have sex with her.

Before she even knew what she was really doing, the blonde somehow knocked on the door. She bounced on her feet gently before almost twisting her ankles when the door opened. Emma would have surely fallen over if she hadn't regained her balance because the sight before her was just... _wow_.

In front of her stood the infamous Regina Mills clad in a purple blouse and black skirt. Emma decided to allow her eyes to drag up the woman's body, showing gratitude to each and every part of her. Black heels and matching stockings covered the woman's legs, and Emma showed her appreciation silently, her tongue darting out to skate over her teeth and lips. Emma's eyes continued up Miss Mills' body, devouring the black skirt that was surely painted onto the woman's thighs and derrière. The eggplant colored blouse had Emma drooling as she took in the sight of one, straining button. It threatened to snap, and ultimately freeing the woman's breasts. Judging by the length of obvious valley on the politician's chest, her breasts had to have been reasonable sized, at least Emma was assuming.

The politician's beauty was just as obvious as her seductive apparel. Charcoal colored hair fell to the woman's shoulders. Regina's dark eyes peered into Emma's green orbs with blatant seduction and smugness. There was a small scar above her lips, and Emma wondered what it'd be like to drag her tongue over it.

"I assume you're my potential victim," the older woman said curiously, eyes now roaming the blonde's body.

Emma nodded and subconsciously pushed out her breasts, which she thought of as her best feature. "I am, unless you're expecting someone else, and in that case, I don't do threesomes," she sassed back.

Regina chuckled once, then twice. "You will _do_ whatever I _pay_ you to do, is that understood?"

The blonde stared at the politician for a moment, completely stunned at the woman's audacity to say such a thing, but Emma should have expected this from Regina _I Purchase Wine Worth More Than You_ Mills.

"Yes?" Emma stuttered out as a question rather than response.

This seemed to amuse the older woman further, which irritated Emma to no depths. Regina Mills gripped Emma's wrist and swiftly pulled her into the hotel room, closing the door with her foot. The blonde stumbled in slightly, now completely annoyed with the woman that she was meant to sleep with. Emma hoped and prayed the woman would just pay her and ask her to leave, even if the politician was stunning and had a nice ass.

_Damn it, Swan_ , Emma thought, _don't mentally compliment the enemy._

"What is your name, dear?"

The smooth, husky voice snapped Emma's attention. She looked at the woman curious, studying the way Regina almost made herself seem taller and haughtier by simply standing a certain way.

The blonde held back a cheeky response and bit her tongue. "Emma."

"And last?" Regina inquired, her tone almost bored.

"That's none of your business."

The dark haired woman laughed heartily before walking deeper into the hotel room. Emma stared daggers at her back before following.

She found Miss Mills pouring herself a glass of wine in a conjoined area considered a kitchen. There was a mini-refrigerator, presumably working stove, microwave, dual-sided sink, and a coffee pot. Hell, that was more than Emma had in her apartment.

Emma watched the woman take a sip, focusing on the way her eye lids fluttered closed and the cords in her neck stretched as Regina tilted her head back. A soft moan escapes the politician's throat, almost setting fire to the blonde on the spot. "Are you gonna pay me so I can leave?" The blonde coughed, interrupting the woman's very obvious display of her pleasure in the beverage.

Regina sat down her glass and licked teeth slowly. "And why would I do such a thing? I paid for your services for the night, and I intend to not let my money go to such a waste."

"Didn't stop you from doing that to those other girls," the blonde muttered.

"Repeat that, dear." The older woman demanded, approaching Emma predatorily. She circled the call-girl slowly, eyes dragging up and down the younger woman's body. Her hand found its way to Emma's waist and coiled around it.

Emma nervously planted her feet firmly on the ground, stubbornly refusing to move. She shook her head and bit her bottom lip anxiously. "So you're not paying me until you've..gotten your money's worth?" The blonde offered instead of the truth.

"No," Regina said simply, removing her hand from Emma. "And now that that is settled, I expect you to fold that dress of yours neatly, place it on the counter, along with your underwear, and wait patiently for me on the bed."

With that, the woman walked into another room, which Emma presumed to be a bathroom. She rolled her eyes and began undressing, mindlessly folding her things.

She couldn't believe this woman. Regina Mills was a haughty, self-righteous bitch. She was completely infuriating with her "holier than thou" attitude, and noble, snotty, aristocratic behavior.

It was especially annoying when the politician referred to Emma as 'dear'. The only people that called the blonde that were elderly men and women that asked her for help in reaching the top shelf at the grocery store, or the disgusting men at the local bars that Emma frequented.

_God_ , Emma thought. She hated this woman, but she had this undeniable desire to throw her on to the bed and ravish her until she screamed the blonde's name. If, no, not if.. When Emma accomplished that, she would successfully knock the high and mighty Regina Mills off of her pedestal. 

As naked as the day she was born, Emma moved over to the bed, leaning over slightly to run her fingers of the satin blankets. She waited on the bed awkwardly, crossing her legs and allowing one hand to cover her breasts. Thankfully she didn't have to wait long as the door to the bathroom opened and out came Regina Mills.

Emma's mouth hung open at the sight of the politician, naked minus black hold-up stockings. Her breast were freed from the confines of her shirt from earlier and that tight skirt had to have been pried from her thighs by the jaws of life. Subconsciously, Emma licked her lips, eyes shamelessly roaming over the woman's tanned, taut skin.

"Do you see something you like, Emma?" Regina purred, stalking towards the bed.

Not trusting her words, the blonde nodded vigorously before shooting up from the bed and reaching out for Regina's body.

The politician tutted, "Oh no, dear. On the bed, on your back."

Doing as told, Emma crawled back on to the mattress and positioned herself on her back, instinctively spreading her legs. This seemed to please the older woman as she followed along, taking residency between Emma's spread thighs.

The blonde's breath hitched as she felt a puff of hot breath greet her overheated and already moistening cunt. She shivered deliciously and threw her head back, blonde hair cascading all over the blankets.

Regina chuckled to herself before repeating the bursts of air, obviously enjoying watching Emma's reaction. Suddenly, Emma jolted up on to her elbows, gasping as she felt a hot tongue swipe at her inner labias. Reflexes caused her to close her legs instantly, but Regina pried them open, digging her nails into milky flesh.

The dark haired woman continued long strokes of her tongue, lapping up Emma's collecting wetness. "You taste so sweet," Regina purred, her breath on the blonde's exposed center sending tremors through Emma's body.

"Oh god," Emma murmured, tossing her head back, eyes glued shut.

The woman between her thighs chuckled and continued, swirling her tongue in and out, around and around, creating intricate patterns with the tip of her tongue as if it were a paint brush or writing utensil. Emma canted her hips, pushing more of herself into the politician's mouth, needing pleasure despite the fact that she hated her with a strong passion.

Regina continued to swirl her tongue around, and eventually, Emma was bucking, begging for release. Just as she was getting ready to climax, the politician exceptionally slowed her pace before stopping all together.

Groaning, Emma lifted her body up, face contorting in complete shock. "Make me come," she growled.

"Not just yet, dear," Regina purred, crawling off of the bed seductively, surely amused with this. "Soon, I promise. But right now, why don't you get on your knees and pleasure me."

Just the way the prestigious woman sounded when she commanded Emma to do something made her even wetter than she already was. And, if doing this meant Emma would be able to come, then she sure as hell would do it.

Once on her knees, Emma pushed her hair to one side over her shoulder and leaned forward to glide her tongue through Regina's folds, glancing up at the woman as she did so.

Regina had her eyes fixated on the blonde, blatant desire burning beneath those almost black pools. Her scarlet lips were slightly parted and charcoal hair disheveled. Her chest heaved, subtly moving her chest. Emma didn't fail to notice that, and almost stopped licking the woman in shock at the erotic way Regina's breasts moved, dusky nipples taut. Oh, what Emma would give to have just one nipple in her mouth.

The woman's hand roughly tangled itself in Emma's hair, pulling at the roots and forcing the blonde to literally inhale Regina's cunt. Emma's nose roughly touched the tip of the politician's clit, eliciting a low growl of pleasure. The woman's hips began canting frantically as Emma pressed her tongue inside of Regina, nose stimulating her clit.

It didn't take long for Regina to come, head thrown back in passion. Her lips parted while desperate, hearty moans emerged from the back of her throat.

She pushed Emma back forcefully, and the blonde tumbled backwards, landing on her back. "What the hell!" The blonde exclaimed, wiping the woman's juices from her mouth with the back of her hand.

"Shut up," Regina demanded, tugging upwards at the blonde's roots. "And get on your hands and knees."

Emma complied with the roll of her eyes. She waited in silence on the bed as the dark haired woman left the room yet again. The blonde rolled her eyes, something she seemed to be doing frequently tonight. The pit of her stomach was burning like a fire, begging to be extinguished but having been denied such a privilege.

Regina soon returned and Emma felt the bed shift beneath here. Almost instantly following that, Regina's chest was pressed against her back. A thick, strap-on was pushing itself against Emma's cunt and she couldn't help but grind herself against it.

"Beg for it, whore," The older woman demanded, lips inches away from Emma's ear. "Beg for my cock."

The blonde moaned loudly, dipping her back to accommodate for the woman against her. "Please give me it," she whimpered, tilting her head to the side to allow Regina access.

"You're hedging. You can do much better than that, Emma." Regina growled.

"Please let me have your cock, Miss Mills."

Seemingly pleased with the response, Regina guided the phallus into the blonde. Emma gasped at the intrusion initially, but was soon rocking her hips in synchronization with the politician's thrusts.

Emma's walls tightened around the appendage for dear life. She panted desperately, moaning and gasping at the forceful thrusts. Regina was practically pounding in the blonde, and Emma was more than happy to receive such treatment. For some reason, she always liked this type of sex better than anything. There was something so... delicious, arousing, about being fucked like a two dollar whore, even if it was by the most infuriating woman Emma ever encountered.

"Harder," Emma gasped, clawing at the blankets.

Her head was yanked back by the roots of her hair, stretching the cords in her neck, and sure enough, Regina thrusted harder into the blonde. Soon Emma's arms gave out and she fell to the bed, ass still high in the air as she came, body shaking like a leaf.

When the aftershocks diminished and the hot-flash of white light cleared, Emma shuttered, the toy being pulled from her cunt. She laid there panting for a moment before coaxing her tired limbs to allow her to sit up. Emma watched as Regina removed the harness from her hips, and once done, stalked back to the bed, determination in her eyes.

"I want another orgasm, dear," she insisted, climbing on to the bed and settling herself on her back. The politician spread her legs wide, giving Emma a to-die-for view of her sopping cunt.

Positioning herself between the woman's legs, Emma licked her lips, but before she could swipe her tongue between each fold, Regina stopped her. "Beg."

"Please," she whined.

The dark haired woman pushed Emma's face into her cunt and breathed out a sigh as the younger woman ate voraciously. "Good girl" she hissed.

Emma looked up from the woman's folds, tongue lapping and swirling desperately. Green eyes glittered in pure devotion, and the blonde was surely admitting now that she was addicted to the intoxicating taste of Regina Mills' cunt.

Regina soon climaxed with a loud groan, hips canting and pressing herself further into Emma mouth. The blonde licked her nectar up carefully, but as soon as the politician caught glance of Emma's mouth, glistening with her come, she pressed her face back down and demanded "Again".

None too happy to oblige, Emma slurped, licked, and sucked, bringing the older woman to yet another climax.

Regina was boneless, but the way the blonde's eyes locked with her own had her desiring more. "One more," she hissed.

Emma closed her eyes and devoured Regina's entire cunt with her mouth, moving her whole head to please the politician. This motion allowed Emma to make exaggerated strokes with the flat of her tongue.

Regina decided that she absolutely loved the way the woman ate pussy, completely devoted, as if she was starving and her cunt was the only source of nutrition available. She planted both feet on Emma's shoulder and began rocking her cunt against the blonde's face, smearing herself of the girl's lips.

Slurping as if it were her last meal, Emma gripped Regina's hips and held her in place, sucking on her clit desperately in order to bring the woman to climax faster.

This seemed to do the trick as the older woman climaxed with a scream, her entire body shaking in Emma's grap. The blonde went to lap up Regina's come, but was pushed away with a weak "Sensitive".

Completely understanding to such a thing, Emma leaned back on her knees and wiped her face. She watched the woman lay there, quivering and panting, then climbed off the bed and began to dress.

"Please stay," stopped Emma in the midst of clasping her bra.

Turning around curiously, the blonde looked at Regina, who was now curled under the blankets and seemed to be asleep. Emma would think the woman was asleep if she hadn't heard her speak.

Against her best judgement, Emma pulled her underwear on and walked back to the bed. She slipped under the covers, and was completely surprised to feel the older woman curl into the blonde's side.

 _Who knew Regina_ I'm a Stuck-Up Bitch That Has to Have Her Own Way and Also Enjoys Rough, Animalistic Sex _Mills was a cuddler,_ ,Emma thought.


End file.
